


Five ways Castiel tried to woo Dean Winchester, and the one time he didn’t need to.

by mrstotten



Category: Supernatural
Genre: Crack, M/M
Language: English
Status: Completed
Published: 2012-06-24
Updated: 2012-06-24
Packaged: 2017-11-08 11:43:17
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,548
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/442856
Author URL: https://archiveofourown.org/users/mrstotten/pseuds/mrstotten
Summary: <blockquote class="userstuff">
              <p>As the Winchesters try to prepare for the apocalypse with hunting and research. Castiel has a different type or research in mind. Crack induced fluff.</p>
            </blockquote>





	Five ways Castiel tried to woo Dean Winchester, and the one time he didn’t need to.

**Author's Note:**

  * For [moonlettuce (Claire)](https://archiveofourown.org/users/Claire/gifts).



** 1\. Learn to love yourself and he will love you. **

 

Sam Winchester was used to his life taking unusual turns. He had died twice, seen both his mother and father after they had died, and had watched his brother die at least a hundred times. Oh, and through his veins ran the blood of a soul sucking, devil worshipping demon who had murdered his mother in order to turn Sam into a soldier of hell capable of resurrecting the devil.

 

So yeah, you could say that Sam was pretty well versed in all things weird and unusual.

 

But over the last few weeks life had went to a whole new level of strange.

 

~*~

 

Sam opened the motel room door, keys dangling from his mouth as he juggled with the coffee and doughnuts in his arms. This was the last time that he listened to Dean’s pleading about how he couldn’t be as efficient a hunter when worrying about his low blood sugar.

 

“Dean?” he called out, the sound muffled by the obstruction in his mouth.

 

He looked around the empty motel room, and stifled a sigh, Great. Letting the keys fall from his mouth, they clattered onto the table. He set down the brown bag and coffee holder and started emptying the bag of its contents. 

 

Opening the box of doughnuts, Sam smiled in satisfaction as he took out the fudge cream, Dean’s favourite. Well, that would teach him to disappear after sending Sam out for the supposedly vital sugar and caffeine rush.

 

Sam kicked his feet up on the table and bit into the doughnut, his tongue chasing the bit of sugary cream that had oozed onto the side of his lip. Just as he went to take the second bite, he heard what sounded like muffled conversation coming from the bathroom.

 

Sam stood up quickly and slid the doughnut under a napkin in case he was wrong that Dean was gone. Even though the doughnut was his by Winchester rules, there was no point in letting Dean see the evidence.

 

Picking up the handgun, he headed towards the bathroom and opened the door smoothly and silently. As the occupier of the bathroom finally came in sight, Sam’s shoulders relaxed and he breathed a sigh of relief. Castiel, although usually the bearer of bad news, was not a homicidal demon. It took Sam a few seconds to take in what Castiel was actually doing, and two more seconds after that for Sam’s relief to turn to utter confusion.

 

“You are a good person; you deserve the best that life has to offer. You are a unique and beautiful soul who deserves a warm and fulfilling love.” Sam watched as Castiel repeated the bizarre mantra three more times before he found any words. “Um... Cas,” Sam interrupted, feeling even more unnerved than ever as the angels eyes met his own in the mirror and Castiel repeated the words again.

 

Sam backed away from the door slightly as Castiel finally turned round and headed for the door to the bathroom. “Hello Sam,” Castiel said with a smile as he exited the bathroom. “Dean has gone out for a short while; he got a message from Bobby.”

 

“Ok,” Sam answered, rubbing his hand awkwardly against his neck he found the courage to look over at the angel again. “Um Cas, what were you doing in the bathroom?” Sam braced himself for any manner of answer, but found the one he actually got confused him even more.

 

“Liking myself, and reaffirming that I deserve only the best that life has to offer,” Castiel replied in a matter of fact tone. The words, much like the words Sam had heard Castiel repeat in the bathroom sounded practised and rehearsed, like someone reading from a script.

 

Sam’s mouth opened and closed several times, before he finally managed a fairly hoarse,“Uh Huh.”

 

Sam grappled desperately for something to say but found himself drawing a complete blank. Before he could form the next question, the door opened, and Dean walked in.

 

“Hey, you’re back,” Dean stated simply. “Where’s my coffee? Hey Cas.”

 

“Dean,” Castiel turned and greeted Dean with a smile. “Sam and I were just discussing how important it is to love oneself.”

 

“Okay.” Dean replied with a smirk. “Well, I’m all for a bit of self love, Cas. But it usually works better with some lotion, cable tv, and without my baby brother in the room.”

 

Sam looked back at the angel his head feeling fuzzy as he tried to make sense of what Castiel was saying, and move on from his brothers self love routines. How the hell did he get himself into this conversation anyway?

 

Sam raised his shoulders in a half hearted shrug, the universal sign of ‘I got nothing’. He watched as Dean looked at him and Castiel one more time before smirking and replying with a quick, ‘whatever works for you Cas,’ before walking towards the table. After picking up his coffee, Dean started to rummage through the goodies Sam had brought back.

 

Sam saw the danger a couple of seconds too late, and wondered briefly if he could go back to the socially awkward conversation with Cas.

 

“Sonovabitch! You ate my doughnut!”

 

** 2\. Make yourself available to him. **

 

The first time it had happened, Dean hadn’t really thought that much of it. It had been handy, useful even having someone around when needed. But now, well now things were starting to get a little out of hand.

 

~*~

 

Dean banged the top of the television in frustration. They were stuck in a damn motel room, hiding out from Lucifer and his minions. All of whom were on a mission to make sure that Dean stopped breathing.

 

The enforced captivity had already been begun driving him mad. Of course, because it was Dean they were looking for and Sam was goto Research guy, Sam was allowed to come and go as he pleased. When Dean had bitched about it, Sam had made that prissy face, and started going on and on about how they were just trying to keep him safe.

 

Figured, his little brother started the apocalypse but Dean is the one grounded.

 

Story of his life.

 

Then, the damn television. went on the blink. Well, if they thought he was staying in the damn room with no cable then they had another thing coming.

 

Castiel suddenly appeared out of nowhere, startling Dean. Before Dean could even mutter a greeting, Castiel walked towards the television and did some sort of hand wavy thing. Castiel turned back to Dean with a smile. “There you go, all fixed.” Castiel stated happily before disappearing again.

 

Dean shook his head and stared at the space where Castiel had vanished from, and then turned his attention back to the television. Flicking through the channels, he smiled happily at the crystal clear picture. Guess having an angel around came in handy after all.

 

~*~

 

That first time had made sense to Dean; that was before they had all the protection spells in place. Castiel had sensed Dean’s frustration and determination to leave the damn motel, so he had fixed the situation.

 

Made perfect sense. But it hadn’t stopped there. Over the course of the next few weeks, Dean found Castiel showing up whenever he was needed.

 

He wasn’t just talking about the fights with demons, and the usual motley crew. Although it the death toll among the good guys was far lighter with an angel on the team.

 

But there were other occasions, too. Dean would find himself craving some home made pie, and Castiel would show up with what was probably the best apple pie that Dean had ever tasted. Another time, Dean was sitting in the iImpala, bemoaning the lack of good rock stations, when Castiel showed up, and waved his hand. All of a sudden it was AC/DC day on Smooth Radio. Later that week, Dean couldn’t find a matching pair of socks..... and so on.

 

Not that it was a bad thing. At the end of the day. Being a Winchester life could suck on occasion, so it was handy having a friendly angel around to smooth the way.

 

Dean decided he should just stop stressing about it. Castiel was a friend, and he was helping a buddy out; nothing weird about that.

 

Stepping out of the shower, Dean reached out for the towel before remembering they had used the last clean ones yesterday.

 

“Damn,” Dean muttered. Before he could open his mouth to shout to Sam for a semi- clean towel, he felt a now too familiar rustle, and a warm and fluffy towel was thrust into his hands. Dean glimpsed a small sighting of Castiels face, lit up with a pleased smile before the angel disappeared again.

 

Dean stood stock still in the bathroom for several seconds, taking in what had just happened.

 

Ok, so it was a little weird.

 

** 3\. Let him know that you are attractive to others. **

 

Sam hadn’t been actively avoiding Castiel or anything. No, not at all; It had just been the case that ever since that strange encounter a few weeks back, Sam had found it easier to let Dean deal with Castiel.

 

Not that this tactic was working this week however. No , for some reason, this week, Castiel had taken all the attention that he normally paid to Dean, and had focused it on Sam. Sam just wasn’t sure why.

 

Sam knew he wasn’t imagining this. Hell, even Dean had commented on it yesterday.

 

~*~

 

“Here you go, Sam,” Castiel set down the warm coffee on the table next to Sam’s laptop with a smile.

 

Sam tried to ignore Dean’s slightly angry glare, quickly taking a sip of the offered coffee. Damn, but it was the best coffee he had ever tasted.

 

“This is great, Cas,” Sam said, smiling up at the angel. “Thanks.”

 

“You’re very welcome, Sam,” Castiel replied with a smile.

 

Sam heard his brother clear his throat, trying to get the visiting angels attention.

 

Castiel disappeared as quickly as he had appeared. He heard Dean huff in frustration and Sam decided the best way to deal with it was to ignore it. They were Winchesters; they were used to ignoring the dancing pink elephants in the room when they wanted to.

 

Turning back to his research Sam ignored his brothers angry mutterings in the corner and continued to sip his coffee. He had to admit, it was a damn fine coffee.

 

~*~

 

Things continued on that way for the next week,. Castiel would show up, sometimes with coffee from heaven, sometimes without. But without fail, Castiel gave Sam his full, undivided attention.

 

Dean had grumbled about it at first, then ignored it or at least pretended to. Until one day after Castiel’s latest visit, he had finally exploded. This has resulted in he and Sam had ended up in a shouting match with accusations flying about Sam apparently stealing Dean’s Angel.

 

“Your angel,” Sam repeated in disbelief. “Did you just call Cas, your angel?”

 

“You know what I damn well mean, Sam,” Dean blustered. “Don’t get smart with me.”

 

“No, Dean,” Sam argued back. “I have absolutely no idea what you mean. So Castiel and I have started talking more. I would have thought you would have been happy about that. We all have to work together, remember”

 

“Well, yeah,” Dean replied. “Of course I’m happy that you’re getting along, but what’s with all the gifts?”

 

“I don’t know!” Sam finally yelled in disbelief. “Didn’t he do the exact same thing with you a couple of weeks ago. I seem to remember you bitching about how weird it was. Maybe he heard you and decided to stop.”

 

“Oh, don’t be ridiculous,” Dean started, his face red with anger. “He didn’t hear anything. You’re trying to....... wait, you really think maybe he heard me saying that?” Dean asked, his face looking more than a little abashed.

 

“I don’t know,” Sam answered, trying to keep his response even. “Maybe.”

 

Dean ran his hands across his face, his face a mixture of frustration and uncertainty.

 

“I didn’t mean to offend him or anything,” Dean finally said. “I just thought it was maybe getting a little strange... or something. Doesn’t mean I didn’t like it,” Dean finished hurriedly.

 

Sam may have been imagining it, but it appeared that his brother’s voice had risen slightly on the last line, as if Sam wasn’t the only person he was talking to.

 

“Well, mention that next time,” Sam stated simply. 

 

“Yeah, maybe,” Dean replied. Sam could see the walls come back up as his brother tried to control his emotions. Sam knew that his brother hadn’t meant to let slip how much this was bothering him.

 

Sam sat down at the table. The best option would be to move on and ignore it. He would deal with whatever came up the next time Castiel visited.

 

~*~

 

The next time Castiel showed up, he had coffee and cheesecake for Sam and a large blueberry pie for Dean. The three of them had sat around for hours tossing back theories back and forth on Lucifer’s new plan of attack.

 

Dean had tried to appear blasé about it, but Sam had been unable to ignore the mega watt smile his brother had carried on his face for the rest of the day. 

 

Sam toyed with the idea of messing with Dean a little, but it had been a long time since he had seen Dean that happy, so instead, he just smiled and went back to his research. 

 

** 4\. Make an effort to share his interests **

 

“A strip club? You’re planning on taking an angel to a strip club.”

 

Dean signed at the indignant tone in Sam’s voice. He knew it had been a bad idea letting Sam know where they were going beforehand.

 

“Yes, Sam,” Dean answered. “I’m corrupting an angel by taking him to a strip club and plying him with an unholy amount of whisky. Your point is?”

 

“We’re in the middle of a damn apocalypse Dean,” Sam retorted angrily. “Or did you just conveniently forget about that?.”

 

“Yeah Sam, I had forgotten that. Thanks for reminding me” Dean replied smartly. “Of course I know it’s the damn apocalypse. We haven’t seen sunshine for nearly two months, no-one knows where fuck Bobby is, we’ve been attacked four times this week and it’s only Wednesday, and oh yeah, there was a volcano eruption in L.A.. So I’m more than aware that the end is damn well nigh.”

 

Dean saw Sam’s shoulders slump and instantly felt bad. Things had been rocky enough between the two of them recently. They were just starting to come back together into some sense of normalcy, and he really didn’t want to fight any more.

 

“Look,” Dean said, his tone contrite. “I’m sorry ok. I was being a dick. I just think... I get that everything is pretty screwed right now. I do get that Sammy. But I just think now, more than ever, we’ve got to just try and carry on as normal, d’you know what I mean?”

 

“I do, Dean,” Sam replied, his voice husky. “I’m just worried Dean. Right now we never know which step might be our last.”

 

“All the more reason to enjoy them while we can,” Dean replied, a trace of his usual cockiness shining through.

 

“Ok,” Sam finally relented with a smile. “But seriously....a strip club. You don’t think maybe that’s the wrong place to take an angel.”

 

“Hey,” Dean interjected. “It was his idea.”

 

“Right,” Sam answered, a smile slowly growing on his face. “Of course it was.”

 

~*~

 

As they walked home Dean thought over the nights events. It had been an interesting night to say the least. Castiel had seemed relaxed enough. But he hadn’t been overly impressed with the ladies. In fact, at times Castiel appeared to be glaring at them. Particularly the ones Dean was speaking to.

 

Although Dean was sure that it hadn’t been deliberate, Castiel hadn’t been the perfect wing man. Everytime Dean has started pulling out the tried and tested charm, Castiel had popped up beside him. His manner to whatever girl Dean had been with ranged from cold to downright rude. Dean knew it wasn’t Cas’s fault; he just had to learn some social graces.

 

Although they had stuck around till the club’s closing Dean’s old school charm had been no match for the however unintentional, awesomely effective cock blocking moves of Castiel.

 

As a result, rather than escorting a nubile young lady home, Dean and Castiel had headed to an all night burger joint, before heading back to the hotel.

 

While they walked in a companionable silence Dean found himself wanting to know what the angel had actually thought of tonight’s events.

“So,” Dean started. “What did you think of the club? You didn’t seem to enjoy it that much.”

Castiel stopped walking, forcing Dean to come to a stop next to him. Raising his eyebrows, Castiel appeared to consider the question carefully.

 

“It’s not that I didn’t enjoy it,” Cas spoke slowly, measuring his words. “It was an experience but there wasn’t much to keep you entertained, after a while.”

 

“Dude, you chose it,” Dean interrupted. “You were the one who wanted to go there.”

 

“I wanted to do something you would enjoy,” Cas replied simply.

 

“Dude, that wasn’t the point,” Dean answered with a frustrated sigh. “The whole point of this was doing something you wanted to do.”

 

“I did,” Castiel replied with a smile. “Let’s just say that I enjoyed the company. Now let’s forget about this. What are the plans for tomorrow night?”

 

Dean smiled and they headed back to the hotel room, with Dean tossing out more and more outlandish ideas for tomorrow nights entertainment.

 

** 5\. Dress to Impress **

 

It had started pretty subtly, in fact it had taken Sam a few days to even notice it. Sam had been researching something on the laptop, when he finally figured it out. “Cas, did you get a haircut?” The question was out of Sam’s mouth before he could stop it.

 

Castiel and Dean both turned away from the map on the table they had been using to mark the rate of demonic activity. Dean’s rose an eyebrow at Sam, but Castiel looked quite pleased.

 

“Yes, I did,” Castiel replied. Sam opened his mouth to ask another question, but the ‘dude what are you on’ look on Dean’s face, made him think twice about it. Turning back to the laptop, Sam thought over the last few days. It wasn’t just the haircut. Castiel seemed to have abandoned the suit and trench coat look that he had been sporting for the last year.

 

Sam raised it again later with Dean, after Castiel had left.

 

“So he’s started wearing clean clothes,” Dean answered. “What’s the problem?”

 

“There’s no problem,” Sam sighed. “I’m just saying, don’t you think it’s a bit strange that he went a full year wearing the same outfit. Now he seems to have robbed a local clothes store .”

 

“Dude, you are paying way to much attention to this,” Dean replied with a shake of his head. “He’s just acclimatising, what? That’s a word.” Dean finished indignantly.

 

Sam was about to retort with something when he was interrupted by the shrill ring of the phone.

 

When Dean got off the phone with news of their newest hunt, Sam put all thoughts of Castiel and his ever changing wardrobe to the back of his mind. For now.

 

~*~

 

Maybe: Now that Sam’s interest in the matter was piqued, he began to notice more and more about Castiel, and not just the angels new fascination with fashion. Even more interesting was that despite what he might have said, Dean was noticing it too.

 

One day Castiel showed up in scruffy denims and a beaten up rock shirt. Dean had then promptly proceeded to fill Castiel in on the history of the band. Next came ripped jeans , with a soft grey t-shirt, and biker boots. Sam had found himself not watching Castiel that day, but watching Dean who was, watching Castiel.

 

A couple of days later, Castiel had shown up wearing worn leather pants and Dean had definitely noticed that, as had half the guys in the gay bar they had been scouting out to gather intel. Seriously, he was beginning to think that Castiel was making these jobs up just to wear these outfits.

 

But they hadn’t found out anything of much interest. Of course, that was mainly due to Dean hovering around Castiel like a possessive Rottweiler, staring down any guy who had come within ten feet of the angel.

 

But it wasn’t until the day that Sam and Dean had come home from a visit to the local police station, and found Castiel in their room, wet and barely covered in a towel that Sam figured out at least one part of the puzzle. Castiel had apologised, and mentioned something about, blood and entrails. Sam waved down his apology and told him not to worry about it. Turning to Dean he had found his brother was slightly preoccupied with a rivulet of water that was making its way down Castiel’s hipbone. 

 

Before Sam could do anything more than barely process that information, Dean had finally looked away and walked over to the table muttering something to Castiel about not worrying about it. Sam turned to Castiel and was surprised to find him smirking.

 

Sam raised his eyebrow questioningly, but Castiel merely smiled and headed to the bathroom to get changed.

 

Sam was stunned as he processed the new information. Dean liked Castiel. Dean liked Cas. Question was, how did Castiel feel?. Sam wasn’t ready to watch his brother suffer any more than he already had.

 

A muffled shout from the bathroom broke Sam out of his thoughts. He heard Castiel from the other side of the door, asking for a t-shirt that he had left on the bed.

 

Sam looked at Dean who was thumbing through a magazine as if he hadn’t heard a thing. Sam may have been fooled if it wasn’t for the fact the magazine was Womans Weekly and the tips of Dean’s ears were bright red.

 

Smiling, Sam headed to the bed and grabbed the soft white t-shirt. As he did so he heard a thump and looked at the magazine that had fallen, out of Castiel’s bag onto the bed.

 

Picking it up, Sam scanned over the article and smiled as things finally started to make sense.

 

~*~

 

“Dean,” Castiel shouted out a greeting as he headed into the hotel room.

 

The room was in total darkness and seemed totally unoccupied. Castiel closed the door behind him, and headed into the room. His eyes were just starting to adjust to the darkness when the table lamp came on.

 

Squinting his eyes slightly at the suddenly too bright light, Castiel waited until his eyes adjusted slightly. Dean was sitting at the table, his hand still on the lamp as he started at Castiel, a small smirk on his face.

 

“Why are you sitting in the dark?” Castiel questioned.

 

Dean’s smile grew wider, but he made no reply. Castiel watched as Dean’s hands moved from the lamp to the magazine next to it. Picking up the magazine, Castiel’s heart sunk to his stomach as Dean began to read the article out loud.

 

“Twenty ways to get your man. Step One: Learn to love yourself.” Dean looked at Castiel and raised his eyebrows. “Well, we’ve already went through my helpful tips on that. Step two: Make yourself available to him.”

 

Castiel stared at Dean as he stated aloud the next three steps, amusement lacing his voice as he gave his own opinions on each of them. 

 

“You know, Cas,” Dean continued. “ I was going to leave this alone and not say anything until you got to Step ten: Show him your imagination. And step sixteen? That definitely has the potential to be fun.”

 

Castiel met Dean’s eyes and relaxed, as he saw amusement and affection in them.

 

“But what I can’t figure out,” Dean continued. “Is why this? Why go through all these crazy steps, to get my attention?”

 

“Well that answers your question Dean,” Castiel replied. “It was to get your attention.”

 

“Who said you didn’t already have it?” Dean retorted.

 

A smile blossomed on Castiel’s face, as he took in the meaning of Dean’s words. “Did I?” Castiel asked.

Castiel got his answer as Dean slowly walked towards him, but stopping just a few inches in front of him. Castiel’s breath hitched in his throat and Dean’s hand slid round the back of his neck, pulling Castiel forward. Castiel heard a soft, hoarse Hell yeah you did before Dean’s lips met his. 

 

The kiss started off slow and gentle, a soft exploration of lips,. But as Dean’s tongue slipped inside Castiel’s mouth, t. The tension inside Castiel finally gave. Grasping Dean’s upper arms, Castiel pushed Dean against the wall. The kiss grew rougher, fiercer, as tongues and teeth clashed. When their mouths finally separated, Castiel buried his head in Dean’s neck, his tongue marking a hot wet stripe from Dean’s collarbone to his ear. As he sucked the lobe of Dean’s ear into his mouth, Castiel slipped his leg in between Dean’s, smiling when Dean groaned and threw his head back against the wall. The soft bang drowned out by Dean’s hoarse oh fuck yeah.

 

Castiel claimed Dean’s lips again while Dean rubbed himself harder and faster against Castiel’s leg. Castiel groaned when Dean’s hands worked at his belt buckle, and wrapped his hand around Castiel’s cock. Castiel continued to use his mouth, nipping and suckling at Dean’s neck to elicit as many cries and groans as he could . When he bid down hard on Dean’s coallarbone, he heard Dean groan loud and long, his head dropping onto Castiels shoulders as he came. Castiel felt his own release only moments later.

 

Castiel manoeuvered them both towards the bed and they laid there, his body wrapped around Dean’s, holding him as their breathing slowly returned to normal.

 

“So,” Castiel whispered into Dean’s ear, as his teeth softly closed around Dean’s ear. “You approved of the clothes then?”

 

Dean turned to face Castiel and smiled. “They’re not bad,” he answered. “Although I kinda liked the whole holy tax accountant look, too.”

 

“So what you are saying?” Castiel said with an answering smile of his own. “Is that I went to all that effort for nothing?”

 

“Nah,” Dean gave Castiel lips a nip with his teeth. “Not for nothing, although you really didn’t have to go to all that effort. There is something we have to work on though.” Dean finished and then started suckling at Castiel’s throat.

 

Castiel moved his head back to give Dean better access. “What’s that?” he asked.

 

Dean looked up at Castiel with a wicked grin on his face. “Your choice of reading material,” he replied.

 

Any answer that Castiel would have given was lost in a loud groan when Dean’s mouth moved further down.

 

Burying his hands in Dean’s hair, Castiel decided that Cosmopolitaon was the best book ever written. Yes, even better than Route 666.

 

The End

**Author's Note:**

> Beta’d by the awesome autumn_lilacs the fastes beta in the west. Thanks to the wonderful darksilvercat for the ideas and encouragement and to darksilvercat and savingfaith333 for all their help and support


End file.
